(2R,3R,4S,5S,6R)-2-[(3R,5R)-5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)heptan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 35bf1e3e-c4d3-4cf0-ba55-8cc57ac3083e
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids > Curcuminoids
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[(3R,5R)-5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)heptan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): COC1=C(C=CC(=C1)CCC(CC(CCC2=CC(=C(C=C2)O)OC)OC3C(C(C(C(O3)CO)O)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)CC[C@H](C[C@@H](CCC2=CC(=C(C=C2)O)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O
• InChI: InChI=1S/C27H38O11/c1-35-21-11-15(5-9-19(21)30)3-7-17(29)13-18(8-4-16-6-10-20(31)22(12-16)36-2)37-27-26(34)25(33)24(32)23(14-28)38-27/h5-6,9-12,17-18,23-34H,3-4,7-8,13-14H2,1-2H3/t17-,18-,23-,24-,25+,26-,27-/m1/s1
• InChI Key: HITNONHMKMEYEQ-NHUQRZGQSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₈O₁₁
• Molecular Weight: 538.60 g/mol
• Exact Mass: 538.24141202 g/mol
• Topological Polar Surface Area (TPSA): 179.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 0.62
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 13

Synonyms

• [(1R,3R)-1-(3-Methoxy-4-hydroxyphenethyl)-3-hydroxy-5-(3-methoxy-4-hydroxyphenyl)pentyl]beta-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6884	68.84%
Caco-2	-	0.8390	83.90%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7858	78.58%
OATP2B1 inhibitior	-	0.8644	86.44%
OATP1B1 inhibitior	+	0.8760	87.60%
OATP1B3 inhibitior	+	0.9371	93.71%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7292	72.92%
BSEP inhibitior	+	0.6479	64.79%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	-	0.5447	54.47%
CYP3A4 substrate	+	0.6068	60.68%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7717	77.17%
CYP3A4 inhibition	-	0.8305	83.05%
CYP2C9 inhibition	-	0.8648	86.48%
CYP2C19 inhibition	-	0.8488	84.88%
CYP2D6 inhibition	-	0.8614	86.14%
CYP1A2 inhibition	-	0.7787	77.87%
CYP2C8 inhibition	+	0.5645	56.45%
CYP inhibitory promiscuity	-	0.8859	88.59%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.7776	77.76%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.9377	93.77%
Skin irritation	-	0.8299	82.99%
Skin corrosion	-	0.9555	95.55%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9133	91.33%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.7843	78.43%
skin sensitisation	-	0.8711	87.11%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.8675	86.75%
Acute Oral Toxicity (c)	III	0.7465	74.65%
Estrogen receptor binding	+	0.7848	78.48%
Androgen receptor binding	+	0.6048	60.48%
Thyroid receptor binding	+	0.5767	57.67%
Glucocorticoid receptor binding	-	0.4767	47.67%
Aromatase binding	+	0.5941	59.41%
PPAR gamma	+	0.6259	62.59%
Honey bee toxicity	-	0.7712	77.12%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.7542	75.42%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.48%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.00%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.09%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.49%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.69%	86.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.84%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.73%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.51%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.41%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.59%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	84.53%	94.73%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.14%	92.62%
CHEMBL2535	P11166	Glucose transporter	83.08%	98.75%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.02%	99.15%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.95%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.16%	94.45%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.81%	90.71%
CHEMBL1255126	O15151	Protein Mdm4	80.66%	90.20%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.63%	92.94%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.49%	89.62%
CHEMBL5555	O00767	Acyl-CoA desaturase	80.37%	97.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.06%	95.56%

Plants that contains it

• Anthriscus sylvestris
• Tacca chantrieri

Cross-Links

• PubChem: 11731236
• NPASS: NPC52277
• LOTUS: LTS0019325
• wikiData: Q105029019